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Top 10 Cherry Plain hotels and places to stay

Blue Vista Motor Lodge
Enjoy a peaceful view from the balcony overlooking a serene grassy area with trees.

Blue Vista Motor Lodge

2.0 star property
9.8 out of 10, Exceptional, (179)
"Clean, beautiful view wonderful service"
The price is £191
includes taxes & fees
20 Aug - 21 Aug
Blue Vista Motor Lodge
The Trail in Adams - Berkshires’ Art Hotel
Cozy cabin with a spacious living area, featuring a glass-top table and comfortable seating, and a separate kitchen area with a refrigerator and microwave.

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (132)
"Stayed only one night Very cosy, quiet place "
The price is £154
includes taxes & fees
31 Jul - 1 Aug
The Trail in Adams - Berkshires’ Art Hotel
The Revival House
Cozy living room with a fireplace, dining area, and high ceiling.

The Revival House

3.0 star property
9.6 out of 10, Exceptional, (7)
"Beautifully renovated historical bed and breakfast that offers historical details along with modern touches. Our room was spacious and very clean and common areas are appointed with great attention to detail. "
The price is £151
includes taxes & fees
31 Jul - 1 Aug
The Revival House
Hotel Downstreet, Ascend Hotel Collection
Two single beds with white linens and blue accents, accompanied by bedside tables and lamps, offer a functional workspace.

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1001)
"Clean,friendly staff and great location."
The price is £142
includes taxes & fees
7 Aug - 8 Aug
Hotel Downstreet, Ascend Hotel Collection
The Porches Inn at Mass MoCA
Traditional buildings with welcoming front porches and easy street access.

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (399)
"I especially like the free EV charging for customers!"
The price is £204
includes taxes & fees
5 Aug - 6 Aug
The Porches Inn at Mass MoCA
Harbour House Inn
Stunning traditional architecture with a central entrance and beautifully landscaped surroundings.

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (51)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
The price is £187
includes taxes & fees
5 Aug - 6 Aug
Harbour House Inn
FairBridge Inn Express
Relax in a spacious room with a large bed, two bedside tables, and a separate bathtub area.

FairBridge Inn Express

2.5 star property
5.4 out of 10, (756)
"Close to our target event a plus"
The price is £59
includes taxes & fees
3 Aug - 4 Aug
FairBridge Inn Express
Holiday Inn Express & Suites Pittsfield - Berkshires
Enjoy a diverse selection of hot and cold dishes at our buffet.

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (4)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is £133
includes taxes & fees
31 Jul - 1 Aug
Holiday Inn Express & Suites Pittsfield - Berkshires
Hilton Garden Inn Lenox Pittsfield
Relax on the patio with wicker sofas and armchairs, surrounded by a fire feature and a beautiful garden view.

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is £172
includes taxes & fees
17 Aug - 18 Aug
Hilton Garden Inn Lenox Pittsfield
Wagon Wheel Inn
Enjoy a serene outdoor setting with two picnic tables on a well-maintained lawn.

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (614)
"Convenient location for my trip"
The price is £58
includes taxes & fees
31 Jul - 1 Aug
Wagon Wheel Inn
Howard Johnson by Wyndham Lenox
Stylish motel with a central entrance and two wings, featuring individual rooms with doors and windows.

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (771)
"Was great loved the jacuzzi tub "
The price is £83
includes taxes & fees
26 Aug - 27 Aug
Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Williamstown
Enjoy a refreshing swim in the backyard pool surrounded by a fence.

Howard Johnson by Wyndham Williamstown

2.0 star property
6.4 out of 10, (859)
"Humble little hotel. Ideal for a visit to nearby Mass MOCA."
The price is £92
includes taxes & fees
6 Aug - 7 Aug
Howard Johnson by Wyndham Williamstown
Berkshire Mountain Lodge
Enjoy cooking in this well-equipped kitchen with a double sink, oven, and gas range.

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (534)
"Excellent stay!"
The price is £104
includes taxes & fees
17 Aug - 18 Aug
Berkshire Mountain Lodge
Hampton Inn & Suites Berkshires-Lenox
Hotel features a two-story design with a flat roof and a mix of brick and siding.

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Good lodgings in a great area to visit."
The price is £142
includes taxes & fees
25 Aug - 26 Aug
Hampton Inn & Suites Berkshires-Lenox
Hotel On North
Enjoy a diverse menu at this restaurant, featuring a selection of drinks and a modern design.

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (746)
"Staff were excellent and welcoming."
The price is £158
includes taxes & fees
3 Aug - 4 Aug
Hotel On North
The Yankee, Trademark Collection by Wyndham
Classic hotel entrance with a covered walkway, surrounded by beautifully maintained gardens.

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1016)
"Loved the Yankee Inn!"
The price is £133
includes taxes & fees
31 Jul - 1 Aug
The Yankee, Trademark Collection by Wyndham
The Central Downtown Inn & Suites
Compact kitchen with modern design, featuring white and wood cabinetry, refrigerator, coffee maker, and toaster.

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (299)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is £108
includes taxes & fees
3 Aug - 4 Aug
The Central Downtown Inn & Suites
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Dine in style with a long table set for a memorable meal, surrounded by cushioned chairs and large windows offering a view of the outdoors.

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (838)
"I like this place a lot and have stayed here many times over the years. Comfortable stay at a reasonable price at a convenient location in Pittsfield. "
The price is £108
includes taxes & fees
17 Aug - 18 Aug
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshires Untold
Relax in a stylish space with a bar area, seating area, and large windows offering views of the outdoors.

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (650)
"It's a clean, nice place. And easy to get to the surrounding towns."
The price is £474
includes taxes & fees
8 Aug - 9 Aug
Berkshires Untold
Courtyard by Marriott Lenox Berkshires
Relax by the fire pit in our outdoor seating area, surrounded by wicker furniture under a covered patio with a flat roof.

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (566)
"After coming to Lenox for 15 years, I can easily say this is the best in town. "
The price is £170
includes taxes & fees
17 Aug - 18 Aug
Courtyard by Marriott Lenox Berkshires
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Learn more about Cherry Plain

Head to Cherry Plain State Park and Brodie Mountain—just two of the sights around Cherry Plain.

See all hotels in Cherry Plain

Top Cherry Plain Hotel Reviews

The Williams Inn

The Williams Inn

10/10 Excellent
"The property was spacious but still had a cozy feel. "
Marcella 1-night trip
Posted 2 days ago
The Williams Inn

Frequently asked questions

Where is the best place to stay in Cherry Plain?

Vacation Village in the Berkshires, located 5.6 mi (9 km) from the heart of Cherry Plain, is a top choice for your stay, based on our traveller data. Two other choices for your stay in the area are Hotel Downstreet, Ascend Hotel Collection and The Williams Inn. See all available top hotels, or vacation rentals in Cherry Plain.

What are some of the best holiday rentals that Cherry Plain has to offer?

Contemporary Berkshire Home with Views of Taconic Golf Course: This holiday home rental outside of Cherry Plain offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. See all vacation rentals in Cherry Plain.

If I need to cancel my hotel reservation in Cherry Plain, will I receive a refund?

Yes, you'll find most room reservations are fully refundable if cancelled before the hotel’s cancellation deadline, which often is within 24-48 hours of check in. If your reservation is non-refundable, you might still have the option to cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Cherry Plain.

What are some hotels with pools in Cherry Plain?

Vacation Village in the Berkshires: 3-star condo, 2-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool and a health club. Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel and Hilton Garden Inn Lenox Pittsfield are a couple of other choices that offer an on-site pool. View all hotels with pools in Cherry Plain.

What is staying in Cherry Plain like?

Visitors to Cherry Plain will definitely find plenty to explore and enjoy. There are 665 hotels and other accommodation options in the surrounding area. Find out more about Cherry Plain.

What should I do while I'm visiting Cherry Plain?

Places to visit in the wider area include Brodie Mountain, Williamstown Theatre Festival and Jiminy Peak Mountain Resort. You'll also find Mountain Coaster and Waubeeka Golf Links in the area. Take a look at what more there is to see and do in Expedia's Cherry Plain guide.

What's the weather like in Cherry Plain?

The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Cherry Plain are January, March, February and November, with each month seeing an average of 18 cm of snowfall.